About: Chemo-enzymatic synthesis of silybin and 2,3-dehydrosilybin dimers

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About: Chemo-enzymatic synthesis of silybin and 2,3-dehydrosilybin dimers Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Divalent or multivalent molecules often show enhanced biological aktivity relative to the simple monomeric units. Here we present enzymatically and chemically prepared dimers of the flavonolignans silybin and 2,3-dehydrosilybin. Their electrochemical behavior was studied by in situ and ex situ square wave voltammetry. The oxidation of monomers and dimers was similar, but adsorption onto the electrode and cell surfaces was different. A 1,1-diphenyl-2-picrylhydrazyl (DPPH) and an inhibition of microsomal lipoperoxidation assay were performed with same trend of results for silybin and 2,3-dehydrosilybin dimers. Silybin dimer showed better activity than the monomer, while on the contrary 2,3- dehydrosilybin dimer presented weaker antioxidant/antilipoperoxidant activity than its monomer. Cytotoxicity was evaluated on human umbilical vein endothelial cells, normal human adult keratinocytes, mouse fibroblasts (BALB/c 3T3) and human liver hepatocellular carcinoma cell line (HepG2). Silybin dimer was more cytotoxic than the parent compound and in the case of 2,3-dehydrosilybin its dimer showed weaker cytotoxicity than the monomer Divalent or multivalent molecules often show enhanced biological aktivity relative to the simple monomeric units. Here we present enzymatically and chemically prepared dimers of the flavonolignans silybin and 2,3-dehydrosilybin. Their electrochemical behavior was studied by in situ and ex situ square wave voltammetry. The oxidation of monomers and dimers was similar, but adsorption onto the electrode and cell surfaces was different. A 1,1-diphenyl-2-picrylhydrazyl (DPPH) and an inhibition of microsomal lipoperoxidation assay were performed with same trend of results for silybin and 2,3-dehydrosilybin dimers. Silybin dimer showed better activity than the monomer, while on the contrary 2,3- dehydrosilybin dimer presented weaker antioxidant/antilipoperoxidant activity than its monomer. Cytotoxicity was evaluated on human umbilical vein endothelial cells, normal human adult keratinocytes, mouse fibroblasts (BALB/c 3T3) and human liver hepatocellular carcinoma cell line (HepG2). Silybin dimer was more cytotoxic than the parent compound and in the case of 2,3-dehydrosilybin its dimer showed weaker cytotoxicity than the monomer (en)
Title	Chemo-enzymatic synthesis of silybin and 2,3-dehydrosilybin dimers Chemo-enzymatic synthesis of silybin and 2,3-dehydrosilybin dimers (en)
skos:prefLabel	Chemo-enzymatic synthesis of silybin and 2,3-dehydrosilybin dimers Chemo-enzymatic synthesis of silybin and 2,3-dehydrosilybin dimers (en)
skos:notation	RIV/61388971:_____/14:00428380!RIV15-AV0-61388971
http://linked.open...avai/riv/aktivita	I P
http://linked.open...avai/riv/aktivity	I, P(GBP303/12/G163), P(LD13041)
http://linked.open...iv/cisloPeriodika	4
http://linked.open...vai/riv/dodaniDat	2015
http://linked.open...aciTvurceVysledku	Valentová, Kateřina Kuzma, Marek Vavříková, Eva Křen, Vladimír Marhol, Petr
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Mikrobiologický ústav AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	7114
http://linked.open...ai/riv/idVysledku	RIV/61388971:_____/14:00428380
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	flavonolignan; silybin; silibinin (en)
http://linked.open.../riv/klicoveSlovo	silibinin silybin flavonolignan
http://linked.open...odStatuVydavatele	CH - Švýcarská konfederace
http://linked.open...ontrolniKodProRIV	[4C8E82DEA4C0]
http://linked.open...i/riv/nazevZdroje	Molecules
http://linked.open...in/vavai/riv/obor	CE
http://linked.open...ichTvurcuVysledku	5 (xsd:int)
http://linked.open...cetTvurcuVysledku	7 (xsd:int)
http://linked.open...vavai/riv/projekt	Centre of drug-dietary supplements interactions and nutrigenetics Supramolecular antioxidants protecting proteins against oxidative damage
http://linked.open...UplatneniVysledku	2014
http://linked.open...v/svazekPeriodika	19
http://linked.open...iv/tvurceVysledku	Křen, Vladimír Kuzma, Marek Vavříková, Eva Ulrichová, J. Vacek, J. Valentová, Kateřina Marhol, Petr
http://linked.open...ain/vavai/riv/wos	000336087800018
issn	1420-3049
number of pages	20 (xsd:int)
http://bibframe.org/vocab/doi	10.3390/molecules19044115

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